Design Your Dream Career with Jess Lane
You spent your whole career building someone else’s brand. What happens when the title, the salary, and the identity get taken away overnight?
In this episode, we have Jess Lane, founder of The Full Cup Co., the career design company for the future of work. After twenty years in marketing and advertising for names like Procter and Gamble, Porsche, and The RealReal, Jess was laid off at forty in a mass reduction and applied to 496 jobs before deciding to build something no employer could take away. She joins us to talk about designing your next chapter, future-proofing your career in the age of AI, and why your worth was never tied to that spreadsheet.
Is the 9-to-5 really going away? It is changing fast. LinkedIn co-founder Reid Hoffman has said the 9-to-5 could be extinct within a decade. The takeaway is not panic, it is that work is being redefined, and there are real ways to future-proof yourself for what comes next.
How do you future-proof your career against AI? Lean into what is most human. Strategy, intuition, creativity, and human storytelling are becoming the most valuable skills. Use AI as a tool, but do not try to sound like it. The more human you are, the harder you are to replace.
What is career design, and how is it different from a side hustle? Career design starts with your unique blueprint, your motivators of autonomy, connectedness, and competence, then builds a sustainable path around your life. A side hustle is usually just extra income without that foundation. As Jess puts it, side hustles are often “hustley,” while career design builds the career meant for you.
How do you financially prepare to leave a stable job? Do not leap and hope. Leaping is not a strategy, an exit plan is. Look at ROI and risk differently, turn the unknowns into knowns, and build a plan with real timelines and numbers. Investing in yourself is what makes the leap sustainable instead of scary.
Ready to design your next chapter? Join us for the next Money Talks. Click here to register for FREE and bring your questions!
Once you have an idea of what you want next, the next question is often: can I actually afford to do it? Our guide to financially preparing for a career change walks through the numbers to put on paper before making the leap.” And link this page you are making for Bill.
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Barbara Provost, EdD and Maggie Nielsen, MBA are the co-founders of Purse Strings, a national platform helping women make confident financial decisions by connecting them with vetted financial professionals who truly understand women’s lives and money needs. Purse Strings connects women across the U.S. with vetted financial professionals who specialize in supporting women through divorce, money transitions, and financial independence.
Full Episode Transcript
(This transcript was generated using AI, so please excuse any misspellings or errors)
[00:00:00] So when I got out of school, or maybe I was still in school, and they tell you to do these like informational job interviews with people, and I talked to this neighbor who I knew worked at one of the Big Four. I think it’s a Big Four. And I was like, I knew this place had like intense job interviews, all this stuff.
And this man was like, “Oh when I went to school, they just gave my resume to this company. The company called [00:00:30] me, hired me, and I haven’t been anywhere else since. So I don’t have an updated resume, and I honestly don’t think I could get the job now if I had to go through the interview process that they have right now.
But I would recommend you just apply.” And I don’t know if it was ’cause he was just an older white man or what, but I was like, “This is insane.” Because now it was like a five-part interview, and this man has been [00:01:00] at this job forever. And I knew then that times were changing. And I’m still just astounded.
I think about him more than I should. But all that to say, times are changing. We don’t have to be loyal to these companies forever because we know we can be fired in a matter of minutes. Just let go because of downsizing, AI, all these different things. And so we wanna be prepared for that next step.
And that’s not hoping for the worst, but it’s planning for what’s next and what fits [00:01:30] our life and what we wanna do. And so I am so excited to have Jess on today as she helps people build this plan for the next step, whether that’s, preparing to leave a company, maybe start a new company, find a job that resonates more, whatever it may be.
But we know nine-to-fives are not as secure as they used to be. We don’t stay at these companies until we die anymore. And so it’s really having that next step, especially if you’re in that mid-career, like 40 to 60. So I think this is gonna be a really exciting [00:02:00] episode, and she’s full of facts and stats and all of that good stuff, which we love.
So tune in, and I can’t wait for you guys to meet Jess.
[00:02:30]
Maggie: Jess, welcome to Women and Money: The Sh*t We Don’t Talk About. And today we are gonna be talking about some sh*t I don’t think we’ve talked about before. So before we dive into all that fun, can you share with our audience who you are, what you do, and what led you to build The Full Cup Co.?
Jess: thank you for having me. My name is Jess Lane. I’m [00:03:00] founder of The Full Cup Co. I call it the career design company for the future of work, and I work with executives who are ready to design their next chapter. So I have a program called the Strategic Executive Exit. That’s a ninety-day program, and basically that is both your landing and your launch pad to design your future of work, and we look at all of your different options, including what’s possible for you outside of a nine-to-five.
Jess: And then I also have a smaller ninety-minute sprint version of that called the Career Design Clarity Session. But all are based in my framework, which is the Full [00:03:30] Cup Method. And that really sits at the intersection of my work of psychology and my marketing background. So the CliffsNotes on how I arrived here are really, I had twenty years in marketing and advertising, and I went from big to small.
Jess: So I started off on Procter & Gamble, Porsche, MillerCoors, and then I went to The RealReal, where we went IPO. The last company I worked for, we reached billion-dollar unicorn status. I led the brand launch for that, and then I was laid off in late 2022 in a mass reduction. So I really rode the high highs and the low [00:04:00] lows, especially at the end with tech.
Jess: I was forty when I got laid off, so between our reflective moments as we get, into that generativity versus stagnation stage, just as humans and human development, plus the market being what it was, I’d applied to four hundred and ninety-six jobs, yeah, when I was let go. And so I was noticing the trends and the data, which I had done for my whole career on behalf of other products, and I was just making the product myself, and I was [00:04:30] looking around and thinking, “Wow, the market has really changed.”
Jess: So I decided personally to get my master’s degree in psychology. It was a life bucket list item for me. And then I founded The Full Cup Co. And like I said, my work is really grounded in the intersection of my background of psychology and marketing to help design that framework to help people design their next chapters.
Maggie: I love it. Yeah, there’s so much to dive into here. I am still, like, just stuck on you applying to all those jobs. I mean, I know even when I got out of school, I, like, went back to the career [00:05:00] company. I think I told you this before, and I was like so I applied to like 100 jobs and didn’t get any yet.”
Maggie: She’s like, “That’s a great start.” And I was like, ” Oh,
Maggie: okay.
Maggie: Not the answer I thought you were gonna give me.” So whoever’s looking for a job out there, keep your head up
Jess: Yeah, well, I think it’s because those numbers look so different than they used to. Yeah. You know? And especially from how our, we grew up just seeing our parents and all of the things, you know? So it’s just it’s the t- change is happening at this sort of like [00:05:30] expedited speed, if you will
Maggie: Right. And so I wanna dive into all of this. So you’ve built, like you said, at the highest levels, Fortune 500, IPO, unicorn companies. What was that moment that you realized that the traditional career path was not gonna be enough for you? Or is that kinda when you were let go and then you’re like, “Wait a minute”?
Jess: I always think everything’s sort of a combination of factors, and I think we’re at this unique moment in time, which it is, and I think everything’s related, which I know you and I have had separate exchanges on careers and finances, of course. But nonetheless, [00:06:00] yeah, it was the market, it was the four hundred and ninety-six jobs moment.
Jess: And as I started to get multiple hundreds into my little job tracker spreadsheet, and I know this is the number because I went back into the spreadsheet. But as I started to get further down that list and just sit with the facts as well as listen. And like I mentioned, so we have the market, we have the human development stage.
Jess: So I was about forty, forty-one when I got let go. When we hit about forty to about age sixty-five, actually, we call that the [00:06:30] generativity versus stagnation stage. That’s based on Erik Erikson’s human development stages. So it’s basically natural human development outside of AI, outside of the current job market.
Jess: So again, you have this layered effect, especially for folks now in midlife. And for me, I also knew it was when I listened to myself and I reclaimed that worth. That would’ve been the third thing, is just really listening. Every cell in my body was saying, ” Don’t go back,” like, “You’re worth more than this spreadsheet is indicating.”
Jess: And we need to maybe pull back [00:07:00] from just the resume, pull back from that identity a little bit, as difficult as that is, and pay attention to what the numbers are telling us. So truthfully, when I got really real with the numbers
Maggie: what did you feel like kind of in your body or, like, how’d you keep going? I mean, h- like, I feel like a lot of people look at that and feel deflated of, like, ” People don’t want me. I’m not worthy,” like these different things when you’ve done all this amazing work.
Maggie: I mean, how’d you not feel down and out?
Jess: Yeah, I think a lot [00:07:30] of it is in the reflection, not only of those experiences and what they meant to you, but also understanding the role that you played in them. And then also a fun little career psychology tactic is you can look at each of those roles and experiences and think about like the micro narrative, like the little story.
Jess: Each of our job roles, right? Like even when we were a barista when we were 16 or whatever we did, right? Like has a little story and has a little ditty about what we loved, hated, what we learned, what have you, what we took away from [00:08:00] it. And I think once I started to do that and realized certainly I’d always worked on teams, and so I never did anything alone-alone, but realized the critical role that I had played and all the value that I’d not only taken away from that, but then also applied in other environments, my themes, what was true for me in every role and in those specific roles and looking at those results, ’cause again, the numbers don’t lie.
Jess: So taking that worth back I think is the biggest thing, and realizing they can take away a title, and yes, they [00:08:30] can take away a salary, but a lot of that value is a lot of commercial value people are sitting on that they don’t realize
Maggie: In c- to kinda know like, well, this is what worked for these big companies, I mean, to hire somebody who’s also been in those companies is like great for that next person ’cause you kinda know the ins and out, what works, what doesn’t, how to test it.
Maggie: I mean, that is so much value there where I’d be like, “Ooh, let’s hire her ’cause she’s worked with these big names. Like she knows what’s going on.”
Jess: You would think definitely some of the brands that I had worked on would have helped me in the next chapter, but I think you’re dealing with a lot [00:09:00] of talented people on the market, and that’s kind of what struck me the most was I was let go with 150 talented peers.
Jess: There are thousands of amazing talented people on the market right now that have decades of experience. And I think some of the irony of this, not to go on a tangent, and you, you drive the bus. But what I will say is I think I sent you that Financial Times article that was all about sort of especially midlifers and there is this associated shame with not being what was used in quotes as unemployable in [00:09:30] midlife.
Jess: And what I think the irony there is, is these folks have the most employable skills in the age of AI because technology is evolving at such rapid speeds, we actually don’t need to be all that technical anymore. We just need to know how to use AI, and we can be trained on how to do that. Our strategy, our intuition, our decades of experience and analyzing and creativity and shaping all of– and telling stories, human stories those are [00:10:00] gonna be the most valuable skills.
Jess: So it’s almost sort of like we’re letting go of the most valuable people, and I think those people are gonna go on to realize their value, just like I did, and go on to create more and different value in the world and figure out how to commercialize that in different ways.
Maggie: Yeah, and part of this article that you were sending that we both read was that about women or, but just people in general, like kind of 40 and over were kind of through AI getting kicked out of the job search, you know. So they weren’t [00:10:30] hiring people older, which I was thinking the same thing of like these are people who have been in business, who know how to talk to others, who’ve like had the experience, and part of me is like, well, maybe they’re worth more and they’re just trying to get a lower price range.
Maggie: But I was just so shocked by that and you know, some of these people were then looking for jobs, blowing through their finances and different things, so kind of had to think about a different way to go about it because it’s like they’re hitting their end of the rope on their savings and that’s unexpected and really the time where we want to keep those [00:11:00] investments invested so we can definitely get out of work by 65 or 70.
Jess: Right. and I think one of the key takeaways to all of that was we have to think differently both about how we plan for our finances and our careers, and they’re intertwined, and we’ve known that. But I think the difference is societally, societally, systemically, we’ve grown up relying on a nine-to-five for that.
Jess: So we’ve sort of outsourced that without even knowing it. I didn’t realize or ever think I’m outsourcing my [00:11:30] worth, I’m outsourcing being the CEO of my business because I’m capping my salary, and I’m putting my faith in someone else. But I should say and when you’re young, it’s wonderful to get experience.
Jess: We need experience, so I don’t regret anything, and I still think it’s wonderful for young people. But yes, specifically this midlife stage we have to think differently, and that’s part of why I think the exit plan is a really good solution and just in general, considering how do I future-proof myself in [00:12:00] a way that doesn’t allow an employer to take everything away from me.
Maggie: It’s definitely not the you stay with a company until you retire anymore, and that loyalty pays off, and all of that stuff that our parents experienced. You know, it’s so different from that. And I know this Reid Hoffman, he said, I don’t know if you guys know him, but the 9:00 to 5:00 will be extinct by 2034, which it’s 2026, so less than 10 years.
Maggie: So for women who have built their whole identity around the corporate career, what does that actually [00:12:30] mean? And should they be scared or excited? ‘Cause I could see a lot of people being like, ” Crap,” or a lot of people thinking this is opportunity, you know. And it’s a little bit more than glass half full or glass empty.
Maggie: But give me your insights here.
Jess: well, if you don’t know who Reid Hoffman is, I didn’t actually be- like, before I started doing deeper research into the field. He’s the co-founder of LinkedIn, so he’s sitting on a ton of data, and I think that’s why we care who he is. You know? He just– He’s sitting on, like, more job data than most humans.
Jess: [00:13:00] And if he says the nine-to-five is gonna be extinct in less than ten years, that’s an interesting statement to me. So it means that work is changing. I think the overall takeaway is that the glass is half full here, right? It certainly depends on how you look at it. It doesn’t always feel that way, and it’s a little bit of both.
Jess: It’s scary. You know, I don’t have a glass ball to predict for you, but if you really sit down and you really look at transferable skills and what we’re looking at in terms of future-proofing ourselves, there are [00:13:30] definite avenues that each and every one of us can take to future-proof ourself, and that looks totally different for everyone.
Jess: So for executives who have built their entire identity around their corporate career, you actually kind of have to flip the script, and step number one is just ditch your resume. That’s really uncomfortable for a lot of people who have especially associated theirselves with their titles and the companies they’ve worked for.
Jess: Instead, you need to start with your unique human blueprint and everything that makes [00:14:00] you, and there’s two reasons why we do this. Number one, following our intrinsic motivators, which we uncover through this unique blueprint, and there’s a process for that is based on decades of research to lead us to more success, longer-term success, and well-being over time.
Jess: Our intrinsic motivators are autonomy, connectedness, and competence. So do we have a choice in it? Does it mean something to us? And are we good at it? Those are [00:14:30] intrinsic motivators. That’s why we start with our unique blueprint. We’re not starting with what company is offering what title or what salary.
Jess: The second reason we do this is monetary, because it’s the best way to differentiate ourselves in the future of work. We do not want to sound like AI. It’s the best way to future-proof yourself. The more human, the better. You can use AI as a tool, but we really have to change the way that we think. So I think the overall takeaway here is flip the script and actually start with yourself versus the [00:15:00] market.
Jess: You can figure the market out, but that is, I think, the key differentiator, and it goes along with the financial planning advice that we’re talking about too, which is start with yourself, don’t outsource it.
Maggie: Yeah, definitely. And it seems like so often people are like, “Well, what jobs are out there? How can I make my resume fit that?” But it’s really doing that backwards of like, “What do I wanna do? What makes me happy?” Because I think there’s sometimes where we work so hard to find a job, and we finally get in there.
Maggie: We’ve been working so hard, we took whatever is available, and then we get that job, and [00:15:30] it’s like, it’s horrible, you know? And it’s like we put in all this energy to find this position that really isn’t a fit because we didn’t look at ourselves first. We just kinda said, “What slots are open, and where could I kinda fit in?”
Jess: Right, and you’re limiting yourself. You know, I kind of use this idea of like why default when you can design? So it’s a yes and. You’re not throwing anything away. You’re just thinking about how do I build something for myself that an employer cannot take away? Risk and ROI look a lot different these days, right?
Jess: It’s like putting your whole pot into a 9 [00:16:00] to 5 that you probably know is not gonna last you your entire career. Now, okay, that changes the game. I think we slowly started to see that as I didn’t take a job for 20 years. I took more jobs like a couple years, five years here, you know. So not not couple month stints, but you know, choppier than say previous generations.
Jess: Like my grandfather worked at a bank for decades and that’s just how it went. And so, yeah, it’s sort of slowly evolved, but now AI is really sort of just expediting that. But yeah, [00:16:30] it’s just a totally different approach.
Maggie: And so how is this kind of like unique blueprint and designing your career based on your unique blueprint different than just starting a side hustle or doing something of that? ‘Cause I feel like there is some differentiation there, and people can kind of mush those together in a way that’s not quite it.
Jess: Yeah, for sure. I think there’s a lot of people and a lot of discussion, and rightfully so, around, like, doing your own thing and just, like exiting corporate or tech and sure, but to your point, [00:17:00] there’s differentiation in a ton of different ways that you can actually do that. I think there’s also a lot of different definitions of side hustles, but usually those are more passions or income streams, and by definition, maybe that someone doesn’t truly have enough time for, or probably rarely has gone through more of this holistic filter of laying that proper foundation for career decision-making, aligning that with the future of work, and designing a sustainable business model against it that also fits around your lifestyle and wellbeing.
Jess: Career design is more [00:17:30] that, you know. Side hustles are usually side hustley. They’re hustley. And they don’t have as much of that thoughtful and purposeful end and therefore aren’t as sustainable, right? But career design looks to design the career that was meant for you because it can only come from you.
Jess: So it’s just a more purposeful and holistic approach that’s meant to last for longer.
Maggie: Well, we’d like something that’s sustainable. You know, that’s always the goal. And so there is a real financial fear, of course, financial podcast, that comes with leaving that stable income, right? [00:18:00] So how do you help women kind of think through this money side of that transition without panicking?
Maggie: I mean, everyone always called them the golden handcuffs, right? But you got that income, you got that insurance, you got the match, you got … I mean, even as an entrepreneur, I’m like, “God, I have to pay my personal into Social Security and then what the company would pay into Social Security when usually the company’s paying that.”
Maggie: So it’s just a lot more things that add up, which makes people fearful reasonably
Jess: Oh my gosh. Well, obviously this is a crux of the conversation and a crux of many [00:18:30] conversations, and most, to be honest, because when we’re thinking about our careers, it’s like our careers are not just our careers. They’re a central pillar, if not the central pillar of our lives just because they dictate so many other things.
Jess: All the things. So I think honoring the fear and knowing that usually fear is the unkn- it lurks in the unknown, and when we move the unknown to the known, that’s helpful, and just kind of acknowledging that is really helpful and having a place for that. [00:19:00] So we use a few different strategies, but I think the first thing goes back to what we mentioned before, which is you have to look at ROI, risk and investment differently than we did before.
Jess: And leaping isn’t a strategy, so I’d never tell you to quit and hope for the best or just go follow your passions. We’re taking a look at, yes, alignment, but then we are taking absolutely a look at the market, and ideally we’re building an exit plan. However, if you don’t have that luxury, we’re getting it done quickly enough that we’re compressing that messy middle [00:19:30] anyway.
Jess: So number one is mindset, looking at ROI, risk, investment differently. And number two is that building an exit plan because that is a strategy, not just leaping or quitting. And I think this idea of investment in yourself before it’s too late is really just important for folks to consider.
Jess: It looks different for everyone. But we oftentimes are giving so much to others that we really need to just think about, okay what is the best [00:20:00] way for me forward and what does the investment in myself look like? And so sometimes that takes a look at looking at our lifestyle and prioritizing or working with a financial planner in more depth to say, “I do wanna go out on my own, and what’s a smart way to approach this while I’m planning my exit strategy?”
Jess: But in short, we open with the five key pillars of wellness to my program, which include financial, and it’s less of a how much money do you have in your bank account, and [00:20:30] it’s more like, how are you feeling about where you are at, and what needs to be true in order for you to move forward? So having folks like you in my back pocket’s really important as well experts to help.
Jess: I think honestly the biggest thing, Maggie, is first thing ROI, risk, and investment look a lot different these days.
Maggie: And so kind of going into business, was there a money belief that you had to completely unlearn to kind of make your leap?
Jess: Yes I think I had to understand that both things could be true at once. [00:21:00] that there was no, no investment lost on the p- on the first 20 years, that we could create value out of that still. It wasn’t taken away with the job title. And I had to look at that investment strategy differently moving forward.
Jess: That was tough. No, I was just… That was tough after 20 years of doing it one way to just really have to look at the reality of things and be like, “I actually [00:21:30] think it’s time to change strategies, and I actually think even though it seems a little wild right now, the numbers are saying that’s actually probably a better strategy.”
Jess: Again, given my specific situation
Maggie: What’s coming up for me is like we make this huge investment in ourselves, like 18 to 21 with college, right? I mean, this could be 50 to $100,000 we invest in ourselves, and then from there on, we just like ride the train until the train kind of pushes us off, [00:22:00] right? And what you’re saying is like redo this investment at 40.
Maggie: I’m not saying maybe $100,000, but like you have to like re-up and re-skill, and we are not the people that we are at 18, and the path might look different and the, the twists and turns might not have led us to where we thought we might be at this time because is anyone where they thought they would be when they were 18 and making those decisions and never worked?
Maggie: Like, it’s so different, and we have no question about making that big investment. But then sometimes people look at us like we’re crazy, older, [00:22:30] taking this turn, doing different education, hiring someone, or we feel guilty about investing that money when to me, that’s the time it makes much more sense.
Maggie: You understand how the world works, what bills are, what income we’re looking for, what we like to do. I mean, there’s so much more grounding there, but no one questions you as much when you’re 18. It’s just this funny dynamic, and so I like when you say investing in yourself. It’s like, let’s do this now again when we understand the world and we’re not just babies.
Jess: Ugh, [00:23:00] I love that, like, comparison to college because, yeah, I, One of the very first podcasts I appeared on, Dr. Matt Markley we talked about, like, some people will spend the equivalent on, like, a winter vacation, and we love a vacation. But it’s interesting when it comes to, yeah, personal or career development or like you’re saying, versus riding the train, and that kind of comes back to some of the, like, defaulting to designing- Yeah
Jess: and just some of, again, where we’re at and how the world of work is changing. But I totally… I couldn’t agree more, and [00:23:30] I think w- what we’re going to probably see is this idea of as people also continue to live longer, I think the idea of a linear career will potentially phase out or just look very different.
Jess: And the way that people go about work is just gonna change drastically. So I think you get to lean into your weird and be a little bit more creative, ’cause that’s what the future of work will reward, and I think that’s freeing. But it does take a lot of like, “Oh, I used to have to be fit into this resume and fit [00:24:00] this,” ba da.
Jess: And it’s like, “No, now we need you to be different.” And so again that, the mindset piece is sort of a weird experience for a lot of people at first, and it sort of takes people a second, I think, who are thrust into it via a layoff, a minute to be like, “Oh,” shake it off a little bit- … and shake it out and get out of the snow globe or whatever the analogy is and be like, “Oh,” you know, kind of look up and think, “Oh, there’s a lot more going on in the world.
Jess: There’s a lot more options than I used to have.” The barrier to entry’s a lot lower to do some other [00:24:30] things, but it does, again, require support and looking at… and different strategies.
Maggie: And so tell us a bit more about how you work with people. Is this to help people, like, launch their own companies, to get into new careers, just kind of have this backup just in case they do get fired? Like, give us a little bit more grounding on, like, really what it is that you help people do
Jess: Well, it’s all of the above because basically it’s your next chapter designed for you by you. I give you a framework that’s based in the best of psychology [00:25:00] and decades of marketing and go-to-market experience. So, basically the framework helps you, again, to identify that unique blueprint and then we go figure out how to wrap it.
Jess: So what makes sense, everything from how we position whatever you wanna offer to what is the actual offering. We hold hands, we prototype it together, we dip our toe in, and then we create that transition architecture, which is part of what we’re talking about, which is financially what needs to happen, time-wise what needs to happen.
Jess: Where are you in the world? Are you still working? You [00:25:30] know, are you laid off and you can start right away? That looks a lot different for a lot of people. And then what are those next steps? So, that’s what that framework looks like. You can do that in 90 days and go from start to finish in 90 days with that.
Jess: Or you can get the preview, because what a lot of people like is, “Hey, I just want my options.” And you can do a career design clarity session, which is more of like a sprint. That’s a 90-minute session. So you have about an hour of pre-work. You go through some of the same upfront, and then you get a future [00:26:00] of work forecast, which is basically like, “Hey, here are some really unique, distinct paths you could take.
Jess: If you wanna move forward and do the full 90 days, great. If not, you have a great idea of actionable next steps you could take to future-proof yourself.” And that’s, again, a 90-minute commitment, which is awesome for people at a much lower price point. And those are the two core components of how I work with folks now.
Jess: And then for folks that are ready to do like a brand build and really wanna go out and like launch their brand into the world, great. There’s a little launchpad that we can do that uses some of my [00:26:30] marketing and really builds that out. But the career design components are really the 90-day and the 90-minute program.
Maggie: And who do you find is like the majority of kind of people taking this? Women similar to you kind of in their 40s trying to figure out what’s next?
Jess: Yeah I’ve been surprised at how many males have been interested as well. But definitely the old Jess for sure has been the majority of folks that I work with. So, I’ve gotten a lot of old coworkers as clients, and I have also found a lot of [00:27:00] clients on LinkedIn that just resonate with the content and me sharing my story.
Jess: So yeah, usually folks that have worked in corporate or tech and are directors, VPs, and have accomplished quite a bit, but they’re looking at the future of work and wondering about that investment and ROI piece and thinking they’ve built a lot and that maybe they could look at what’s next for them but they’re not sure where to start.
Maggie: I was only in corporate for a little bit, but my favorite thing was just to get rid of all the corporate clothes. All the button-down shirts that weren’t me, all these, like, dress pants [00:27:30] that I would never wear. I was just like, this was just a person they wanted me to fit into, and that’s not me.
Maggie: And it was just like com- coming out of there, I was like, “Actually, if I run my own business, I can wear whatever I want, and it’s not gonna be these gross dress pants.”
Jess: freeing things. When I think about peace and freedom, I’m like, “You know what? I just don’t wanna be rushed to walk my dog.” You know, and that reminds me, I’m like, yeah, like I don’t need the, the dress pants are not necessary. I love the dress pants thing too, because that’s such a real thing. The other thing you just being free, I think, to make your impact.
Jess: You know, [00:28:00] like I’m able to say what I wanna say on LinkedIn because I think it helps a lot of people. And another thing that you just said too was like, this is just it. Like that reminded me is like, this is just an act, and when you think about the idea of like performance leadership or performance reviews, it’s like a performance is a performance. It’s an act.
Maggie: no actor. That’s not
Jess: Yeah. You’re wearing dress pants because you’re acting in a role, you know? And so, yeah, it is. It’s like, it’s interesting ’cause we’re [00:28:30] showing up playing these roles, and to a certain extent we’re filling a job description, but with it comes all of this other stuff and then we become this person that we’re like, “Wait a minute.
Jess: What?” So you can see how that happens because we’re using terminology that like encourages it almost.
Maggie: Definitely. And so for a little like action step for those listening right now who know something needs to change but doesn’t know where to start, what are like one, two, maybe three steps they could take this week to start moving forward?
Jess: Yeah, I think definitely get [00:29:00] in touch with your values and then I think do a little bit of that career narrative exercise just to reflect on meaningful experiences that you’ve had. Think about also life experiences, because the biggest way that you can differentiate yourself in the future of work is going to be that unique blueprint times a human problem that you can solve.
Jess: So I think if you do the values, the unique blueprint, and thinking about what types of problems you care about solving those are some really good things to get in touch with, as well [00:29:30] as looking at some of the practical nature of where are you with your finances and just your overall well-being and doing a little bit of a energy check as well as reality check there.
Jess: Because if you combine both sort of how you’re feeling with the realities of what are in front of you, those are uncovering some things that we don’t think about every day and allowing you the freedom to go from there. Acceptance and understanding where we’re at is a first step to move forward, and I [00:30:00] think that sometimes can remove some of the barriers to even taking the best next step, which is to just understand where we’re at honestly.
Maggie: That’s a big one. I mean, just knowing where you are. Some people, I mean, we always talk about this, like even on your money and your income, people are like, “I actually don’t wanna look in my bank account.” And I’m like, “Well, I can’t say you’re gonna improve if we don’t have a measuring goal of where we started, and maybe the number’s low, so we could easily boost it up.
Maggie: Like, who knows what it is?” Or maybe you’re pleasantly surprised is also, I’m like, it could be way better than you [00:30:30] imagine. You just never know.
Jess: Yeah. But you have to start somewhere. So yeah, I think it, it sounds very basic, but sometimes with busy professionals and life gets busy, It’s harder to make the time to just listen and kinda check in on where we’re at. But then at least you know where you are, and you can go from there
Maggie: So Jess, there is a question we like to ask all our guests before we wrap up. And now with everything that you’ve been through and now being an entrepreneur, what does financial freedom look like to you?
Jess: I think it’s the [00:31:00] ability to be able to take control of your livelihood and your wellbeing and not have to default or outsource that
Maggie: I love it. Nice and simple. I love that. Well, thank you so much for coming on today and sharing your expertise. Of course, we’ll have links to all your information in the chat so people can connect with you just follow you on LinkedIn, have those 90-minute sessions or do that 90-day program.
Maggie: And yeah, we appreciate you, yeah, coming on and doing all the work that you’re doing as it is a changing world, especially with AI, and so we are [00:31:30] excited to have someone who can help us stay on top of it
Jess: Thank you so much for having me. It’s been awesome.
Maggie: Of course. And until next time, listeners, be financially fearless
[00:32:00]
